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With the series being a Long Runner, it’s no surprise that a timeless show like The Simpsons can have many hilarious moments through its time. But then there are these moments that doesn’t quite hit the same amount of hilarity when viewed today.

  • One of the last scenes of "New Kids on the Blecch" depicts the MAD building being blown up after (almost) publishing an unflattering satire of Bart, Milhouse, Nelson, and Ralph. This episode aired seven months before 9/11, and that scene ended up getting cut in some syndicated broadcasts for a while as a result. Also in January 2015, the headquarters of French satirical magazine Charlie Hebdo were attacked by terrorists for publishing a satirical image relating to Islam.
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  • In Season 5's "$pringfield", which aired on December 16, 1993, two No Celebrities Were Harmed versions of Siegfried & Roy perform an act with a white tiger riding a unicycle. The act goes horribly wrong when the tiger attacks both illusionists due to the mistreatment that she has suffered. A decade later, a white tiger actually did attack Roy during one of their shows. The DVD commentary declared it the "greatest prediction ever made by The Simpsons", though the writers also pointed out that the tiger attack was bound to happen sooner or later, considering how she was treated.
  • In the Season 10 episode "Sunday, Cruddy Sunday" (which aired after Super Bowl XXXIII on January 31, 1999), Nelson asks if the postman has ever gone on a rampage and killed people. The postman remarks that the disgruntled mailman stereotype is a thing of the past. Principal Skinner then replies, "I'm glad I work in an elementary school!". This episode premiered when the trend of kids going ballistic and opening fire at their schools was a hot topic, and with one of the most infamous school shootings of all — Columbine — taking place just a few months after it aired, the joke's darkness gets blacker and a lot more tasteless.
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  • There's a scene in "Marge vs. Singles, Seniors, Childless Couples and Teens, and Gays" where Bart wants to watch a TV show where Steve Irwin gets mauled to death by an animal. On September 4, 2006, Irwin died when a stingray pierced his heart.
  • A lot of the earlier episodes had verbal jokes and sight gags depicting Homer as a monkey. In addition, he was often called a "big ape" due to his crass behavior and informed ugliness. These stop being funny with "The Color Yellow", which reveals that one of Homer's ancestors was a black slave.note 
  • The Season 5 episode "Lisa vs. Malibu Stacy" has a scene where Grandpa admits to stealing Andy Griffith's medication for a heart condition while the latter, who's in character as Matlock, is being rushed to the hospital in an ambulance next to the bus Grampa is in. On July 3, 2012, Andy Griffith died of what was later determined to be a heart attack.
  • "Lisa's Date with Density":
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    • Lisa asks Milhouse to send Nelson a love note from her, but Nelson is led to think the note's from Milhouse himself. Cut to Milhouse being led away in a stretcher to an ambulance, with the paramedics telling Lisa that Milhouse can't hear her.note  It really stops being funny after the highly publicized rash of suicides and murders from bullying, especially anti-gay bullying. The setup of the scene is horrifyingly very similar to the murder of Lawrence King in 2008.
    • Nelson's version of "Joy to the World" (where a teacher suffers a gruesome death by the kids' hands) becomes much less funny to UK viewers in light of a teacher being stabbed to death by a student during a lesson in April 2014.
  • "A Totally Fun Thing That Bart Will Never Do Again" centers on Bart sabotaging a cruise ship so his cruise vacation can last forever, which leads to disaster.
    • In February 2013, a similar situation happened to Carnival Cruise Line's Triumph.
    • The episode has Bart hijacking the ship's public address system with a movie clip that causes everyone to believe that there is a worldwide pandemic and that ships cannot head towards land, stranding the passengers in the middle of the ocean in miserable conditions. Fast-forward to 2020, the novel coronavirus outbreak leads to a real life worldwide pandemic, and in one famous case during the early days of the outbreak, the Diamond Princess cruise ship that took a stop in China was left to wander around in the sea unable to dock at any country's ports for fear some of the passengers onboard may be infected. They were eventually allowed to dock in Japan, with the whole ship locked down, all the passengers kept in quarantine, and several passengers and crew members did test positive for the virus..
  • In the Season 7 clip show episode "The Simpsons 138th Episode Spectacular", the original three Simpsons showrunners-cum-creators are Matt Groening (depicted as a gun-crazy redneck), James L. Brooks (depicted as being very fat, very rich, and the winner of several awards), and Sam Simon (depicted as a frail expy of Howard Hughes in his later years). Simon was diagnosed with terminal cancer in early 2013 and died two years later.
  • In "A Star Is Burns", the crossover episode with The Critic that Matt Groening hated, there is a scene from Rainier Wolfcastle's horrible stand-up comedy movie where his Woody Allen "impression" is just Wolfcastle saying, "I'm a neurotic nerd who likes to sleep with little girls." Back then, it was a Take That! at him marrying his stepdaughter, Soon-Yi. Things got worse, when in October 2013, his adopted daughter, Dylan, alleged he sexually abused her twenty years earlier.
  • The "Treehouse of Horror XII" segment "Hex and the City" features a helicopter crashing into Moe's Tavern, killing Lenny and Carl. Twelve years later, a police helicopter did just that in Scotland.
  • In "Treehouse of Horror IX" there is the mention that one of the series also produced by World's Deadliest Executions was titled Secrets of National Security Revealed. In 2013, Edward Snowden stepped down from the NSA after outing himself as the man who revealed the more controversial methods used to gain information at the NSA.
  • A scene in "Lisa the Beauty Queen", normally cut out for syndication, shows Otto operating a faulty rocket ride and after causing it to spin faster at Bart's request, one of the rockets falls off and crashes into the school. 20 years later, Australia was plunged with two fatal accidents with theme park rides. In 2014, an eight-year-old Malaysian girl was thrown off a ride and killed at the Royal Adelaide Show. Two years later, four people were killed in a collision on the Thunder River Rapids Ride at Dreamworld. Poor safety was blamed for both incidents.
  • In "I've Grown A Costume on Your Face" from "Treehouse of Horror XVI", Chief Wiggum becoming 'Jared from the Subway ads' and referring to himself (Jared) as 'sexually ambiguous' is a lot more uncomfortable since Jared Fogle's arrest for child porn possession.
  • In "Ice Cream of Margie (with the Light Blue Hair)", Homer forces a lactose-intolerant boy to eat an ice-cream bar, causing him to collapse as he tells Homer to call the number on his bracelet (Homer then mocks him for the bracelet before finding out it's the number for a doctor). In 2017, an allergic toddler died when his preschool allegedly forced him to eat a grilled cheese sandwich.
  • "Mr. Lisa's Opus" has Bart making a crack that Lisa has "a voice that would make a rhino want to shove its horn in a socket", and then another that Homer is a hippo after Lisa responds to him that rhinos are extinct. Come March 20, 2018 when the last male northern white rhinoceros had died, making the subspecies functionally extinct.
  • In "Viva Ned Flanders", the people running away from the dust cloud after Mr. Burns' casino gets demolished, looks eerily similar to the cloud caused by the collapse of the Twin Towers, two years after the episode was aired.
  • In "The Twisted World of Marge Simpson", at a Springfield Isotopes game, Springfielders are so angry at Mr. Burns "winning" the raffle that they start throwing Marge's pretzels at him, littering the field and hurting Whitey Ford. During a 2001 NFL game with the Jacksonville Jaguars vs. the Cleveland Browns, the NFL referees controversially overturned a potentially game-winning play for Cleveland, making Cleveland fans so angry that they threw bottles and other objects at them with numerous injuries, leading to the game being dubbed "Bottlegate".
  • An example that happened quickly after it came out: in "Team Homer" Homer is shown having stolen the Academy Award for Best Supporting Actor given to Dr. Haing S. Ngor for The Killing Fields. Only a month after it first aired, Dr. Ngor was murdered, which would imply Homer killed him for it. In syndication and on the season seven DVD set, the scene was changed to show the Oscar being the one given to Don Ameche for Cocoon, who had died a few years earlier, but of natural causes.
  • In "Mr. Plow", Homer imagines getting hired by then-President George H. W. Bush to deal with protestors outside the White House, with Homer saying "Mr. President, those young people are about to get a dose of reality" before plowing down protestors with his plow truck. In August 2017, a white supremacist march in Charlottesville ended with a white supremacist plowing down counter-protestors with his car, killing one person and injuring at least 19 others.
    • In a double whammy, the scene was also mirrored in an incident on June 1st, 2020, when a crowd of peaceful protesters outside the White House was forcefully cleared out by federal officers so that Donald Trump could cross the street for a photo op.
  • In Bart vs. Thanksgiving Lisa makes a diorama of important women, including Majorie Stoneman Douglass. She tells Maggie that "you probably haven't heard of her." After the 2018 shooting at Majorie Stoneman Douglass High School, most of America is familiar with that name.


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